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The New Salicylaldehyde S,S-Propanedithioacetal Ester Enables N-to-C Sequential Native Chemical Ligation and Ser/Thr Ligation for Chemical Protein Synthesis
- Source :
- Journal of the American Chemical Society. 142:8790-8799
- Publication Year :
- 2020
- Publisher :
- American Chemical Society (ACS), 2020.
-
Abstract
- The combination of distinct peptide ligation techniques to facilitate chemical protein synthesis represents one of the long-standing goals in the field. A new combination ligation method of N-to-C sequential native chemical ligation and Ser/Thr ligation (NCL-STL) is described for the first time. This method relies on the peptide salicylaldehyde S,S-propanedithioacetal (SALPDT)-ester prepared by a new 1,3-propanedithiol-mediated reaction. The peptide SALPDT-ester, which is compatible with NCL, can be fully activated by N-chlorosuccinimide (NCS)/AgNO3 in aqueous solution to afford peptide SAL-ester for use in the subsequent STL. The practicality of the combined NCL-STL method is illustrated by the synthesis of S-palmitoylated matrix-2 (S-palm M2) ion channel from Influenza A virus and S-palmitoylated interferon-induced transmembrane protein 3 (S-palm IFITM3). This approach expands the multiple-segments peptide ligation toolkit for producing important and complex custom-made protein samples by chemical protein synthesis.
- Subjects :
- chemistry.chemical_classification
Aqueous solution
Stereochemistry
Peptide
General Chemistry
010402 general chemistry
Native chemical ligation
01 natural sciences
Biochemistry
Catalysis
Transmembrane protein
0104 chemical sciences
chemistry.chemical_compound
Colloid and Surface Chemistry
Salicylaldehyde
chemistry
Protein biosynthesis
Molecule
Ligation
Subjects
Details
- ISSN :
- 15205126 and 00027863
- Volume :
- 142
- Database :
- OpenAIRE
- Journal :
- Journal of the American Chemical Society
- Accession number :
- edsair.doi...........3a4de87c226d9a32fcb95b03a6e7d825